Cyclopentyl-(2-methylallyl)-acetic acid



GYQLQPENTYL- (Z-MFET-PHYLAELYL) -A 'GETIC AGED #UNHTE Robert B. Moffett, Kalamazoo, Mich and Charlotte Anne Hart, Kansas City, Mo, assignors to George A. Ereon and Company, Kansas City, Mo a corporation of Missouri No Drawing. Application February 8, 1949, Serial No. 75,303

2 Claims. (Cl. 26il5l4) l 2 This invention relates to cyclopentyl-(Z-rneth- 170 C. until carbon dioxide ceased to be evolved. ylallyl) acetic acid having the formula Distillation at reduced pressure gave 15 g. of cyclopentyl-(2-methylallyl) -acetic acid, B. P. 86 C. (0.04 mm); n =l. io9-i; d4 =0.9768. Calcd. for C11H18021 N. E. (neutral equivalent), 182.25; MD, 51.92. Found: N. E., 180.1; MD, 51.98. (3112 When cyclopentyl-(2-methylallyl) -acetic acid 0132:0-(3113 is treated with a solution of one equivalent of and to salts thereof sodium hydroxide or sodium carbonate or sodium Theme substances of invention are useful bicarbonate, sodium cyclopentyl-(Z-methylallyl)- as intermediates for prepay-mg antispasmodics acetate is produced in solution and can be iso- Moreover, the free acid and its salts with nonlated by evaporation of the Solutiontoxic cations are also useful as bile flow stiinu- The instant application is a continuation in lants. A water-soluble salt is particularly adapted Part of our D pateflt app c al for the latter purpose. and such asalt is prepared 643330, filed January 25, 1946, now abanby reaction of :ie acid with an equivalent amount donedof an appropriate base, preferably an alkali metal We Claim: hydrox'de, carbonate or bicarbonate. A member of the group conslstmg of cyclonew Compounds can be prepared as entyLQ-methylallyl)-acetic acid having the scribed in the following example. 191mm?" Example I (a) methyl cycl faentyl- (Z-methyZaZZyZ) -maZ0- 0011 note. To a stirred suspension of 5.75 g. (0.25 m.) (311 of powdered sodium in 50 ml. of dry toluene was CH I CH slowly added 5? e. of diethyl cy-clopentylmalonate. 3 After nearly all of the sodium had reacted at and non-toxic salts of said acid. reflux temperature, 34 g. (0.375 In.) of Z-rnethyl- 2. CYclopentyl (Z-methylallyl) acetic acid allyl chloride was added dropwise and the mixture having the formula I was refluxed for sixteen hours. After cool ng, the e miXtrre-v-Jas neutralized with dlute acetic acid, and the toluene layer was washed with water, *CHAJOOH dried over anhydrous sodium sulfate and concentrated. The residue was distilled at reduced pres- CH sure, first through a Ciaisen head and then redis- CH2:(]JO}I3 tilled through an efficient fractionating column. The roduct distilled at 71 C. (0.91 min), g ving 49.5 g. of diethyl cyclopentyl-(2-methyla1lyl) malonate; z :1. l-8l3; d4 =1.017().

MD (molar refraction): Calcd. for GIG-H2604, so

ROBERT MOFFETT. CHARLOTTE ANNE HART.

REFERENCES CITED 76.75; fou 1 5 531 The following references are of record in the b) L C W ZJZ-(Z-meZhyZaZZg Z)-acetic acid.-- file of this ratentr A mixture of g". (BASS m.) of diethyl cyclo- UNITED STATES PATENTS pentyl -(2-meth vlallyl) -malonate with a solution n I l or .0 g. 0.1 potassium hydroxide in 106 m1. of ethdo Fg Ad g Jul fi ancl was heated in a bomb at 140-150" C. for three 6 S M 1929 hours. After cool ,most of the alcohol was disams h illed off, water was to the residue and the whole neutral'zed with hydrochloric acid. The FOREIGN PATENTS substituted inalonic acid was extracted with ether, Number Country Date the ether extracts were washed with water 728,998 France July 1932 and with saturated sodium chloride solution containing 21 little sodium bicarbonate, and finally OTHER REFERENCJLS dried over anhydrous sodium sulfate. The ether Perkins et al., J. Am. Chem. $00., vol. 49, pp.

was then distilled off and the residue heated to 2 (19 (Copy i C 

1. A MEMBER OF THE GROUP CONSISTING OF CYCLOPENTYL-(2-METHYLALLYL)-ACETIC ACID HAVING THE FORMULA 